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organic compounds
The amido O atom in the title molecule, C16H11Cl2N3O, is the hydrogen-bond acceptor for the amide group and amine groups of two adjacent molecules; the hydrogen-bonding interactions result in a layer motif.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037196/hb2147sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037196/hb2147Isup2.hkl |
CCDC reference: 624706
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.155
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.813 0.905 RT(exp) = 1.113 PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.12 PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 5.08 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
5-Chloro-1H-indole-3-carbaldehyde 4-chlorobenzoylhydrazone top
Crystal data top
C16H11Cl2N3O | F(000) = 680 |
Mr = 332.18 | Dx = 1.465 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3416 reflections |
a = 8.7172 (8) Å | θ = 2.5–24.5° |
b = 8.6686 (8) Å | µ = 0.44 mm−1 |
c = 19.960 (2) Å | T = 295 K |
β = 93.202 (1)° | Irregular fragment, yellow |
V = 1505.9 (2) Å3 | 0.49 × 0.47 × 0.23 mm |
Z = 4 |
Data collection top
Bruker APEX-II area-detector diffractometer | 2181 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 27.5°, θmin = 2.0° |
φ and ω scans | h = −11→10 |
13557 measured reflections | k = −11→11 |
3423 independent reflections | l = −25→25 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0675P)2 + 0.7475P] where P = (Fo2 + 2Fc2)/3 |
3423 reflections | (Δ/σ)max = 0.001 |
207 parameters | Δρmax = 0.46 e Å−3 |
2 restraints | Δρmin = −0.63 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.10014 (11) | −0.33525 (10) | 0.52693 (4) | 0.0853 (3) | |
Cl2 | 0.34286 (13) | −0.30193 (11) | 0.69859 (8) | 0.1215 (5) | |
O1 | 0.3703 (2) | 0.3651 (2) | 0.45289 (8) | 0.0683 (6) | |
N1 | 0.4325 (3) | 0.3636 (2) | 0.56324 (9) | 0.0536 (6) | |
H1n | 0.477 (3) | 0.4505 (19) | 0.5581 (14) | 0.064 (8)* | |
N2 | 0.4598 (2) | 0.2768 (2) | 0.62142 (9) | 0.0478 (5) | |
N3 | 0.6699 (3) | 0.2077 (4) | 0.83407 (11) | 0.0739 (8) | |
H3n | 0.719 (4) | 0.212 (4) | 0.8720 (10) | 0.109 (13)* | |
C1 | 0.2964 (3) | 0.1425 (3) | 0.51291 (11) | 0.0467 (6) | |
C2 | 0.3214 (3) | 0.0337 (3) | 0.46364 (12) | 0.0556 (7) | |
H2 | 0.3799 | 0.0597 | 0.4277 | 0.067* | |
C3 | 0.2602 (3) | −0.1125 (3) | 0.46754 (13) | 0.0595 (7) | |
H3 | 0.2782 | −0.1853 | 0.4347 | 0.071* | |
C4 | 0.1724 (3) | −0.1499 (3) | 0.52033 (13) | 0.0562 (7) | |
C5 | 0.1416 (3) | −0.0423 (3) | 0.56857 (13) | 0.0586 (7) | |
H5 | 0.0794 | −0.0675 | 0.6033 | 0.070* | |
C6 | 0.2042 (3) | 0.1033 (3) | 0.56461 (12) | 0.0530 (6) | |
H6 | 0.1842 | 0.1762 | 0.5972 | 0.064* | |
C7 | 0.3683 (3) | 0.2975 (3) | 0.50756 (11) | 0.0518 (6) | |
C8 | 0.5310 (3) | 0.3459 (3) | 0.67027 (11) | 0.0477 (6) | |
H8 | 0.5584 | 0.4490 | 0.6664 | 0.057* | |
C9 | 0.5682 (3) | 0.2629 (3) | 0.73131 (10) | 0.0479 (6) | |
C10 | 0.6527 (3) | 0.3190 (4) | 0.78671 (12) | 0.0618 (7) | |
H10 | 0.6919 | 0.4185 | 0.7908 | 0.074* | |
C11 | 0.5994 (3) | 0.0760 (4) | 0.81107 (12) | 0.0648 (8) | |
C12 | 0.5856 (5) | −0.0678 (5) | 0.84100 (17) | 0.0917 (12) | |
H12 | 0.6275 | −0.0857 | 0.8842 | 0.110* | |
C13 | 0.5095 (5) | −0.1824 (5) | 0.8058 (2) | 0.0976 (13) | |
H13 | 0.5016 | −0.2800 | 0.8247 | 0.117* | |
C14 | 0.4434 (4) | −0.1534 (4) | 0.74153 (18) | 0.0771 (9) | |
C15 | 0.4536 (3) | −0.0125 (3) | 0.71096 (14) | 0.0586 (7) | |
H15 | 0.4087 | 0.0046 | 0.6682 | 0.070* | |
C16 | 0.5336 (3) | 0.1048 (3) | 0.74591 (11) | 0.0503 (6) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1104 (7) | 0.0644 (5) | 0.0805 (6) | −0.0241 (4) | −0.0011 (5) | −0.0131 (4) |
Cl2 | 0.1040 (8) | 0.0555 (5) | 0.2073 (14) | −0.0108 (5) | 0.0305 (8) | 0.0093 (6) |
O1 | 0.0968 (14) | 0.0729 (12) | 0.0325 (8) | −0.0167 (11) | −0.0200 (9) | 0.0119 (8) |
N1 | 0.0785 (15) | 0.0476 (12) | 0.0327 (10) | −0.0082 (11) | −0.0141 (9) | 0.0079 (9) |
N2 | 0.0610 (12) | 0.0500 (11) | 0.0308 (9) | −0.0044 (9) | −0.0095 (8) | 0.0045 (8) |
N3 | 0.0828 (18) | 0.108 (2) | 0.0296 (11) | 0.0145 (16) | −0.0107 (11) | 0.0052 (13) |
C1 | 0.0522 (13) | 0.0534 (14) | 0.0332 (11) | 0.0022 (11) | −0.0099 (10) | −0.0020 (10) |
C2 | 0.0629 (16) | 0.0686 (17) | 0.0345 (12) | −0.0028 (13) | −0.0032 (11) | −0.0059 (11) |
C3 | 0.0646 (16) | 0.0644 (17) | 0.0485 (14) | 0.0034 (14) | −0.0052 (12) | −0.0179 (12) |
C4 | 0.0586 (15) | 0.0575 (16) | 0.0511 (14) | −0.0049 (12) | −0.0083 (12) | −0.0103 (12) |
C5 | 0.0604 (16) | 0.0675 (17) | 0.0480 (13) | −0.0118 (13) | 0.0043 (11) | −0.0097 (13) |
C6 | 0.0545 (14) | 0.0609 (16) | 0.0432 (13) | −0.0005 (12) | −0.0015 (11) | −0.0126 (11) |
C7 | 0.0627 (15) | 0.0569 (15) | 0.0341 (11) | 0.0004 (12) | −0.0119 (10) | 0.0011 (11) |
C8 | 0.0604 (15) | 0.0492 (13) | 0.0324 (11) | −0.0041 (11) | −0.0068 (10) | 0.0026 (10) |
C9 | 0.0526 (14) | 0.0605 (15) | 0.0298 (10) | −0.0016 (11) | −0.0035 (9) | 0.0020 (10) |
C10 | 0.0680 (17) | 0.081 (2) | 0.0354 (12) | −0.0027 (14) | −0.0073 (11) | −0.0017 (12) |
C11 | 0.0711 (18) | 0.087 (2) | 0.0368 (12) | 0.0231 (16) | 0.0069 (12) | 0.0182 (14) |
C12 | 0.106 (3) | 0.112 (3) | 0.0594 (19) | 0.045 (2) | 0.0286 (18) | 0.046 (2) |
C13 | 0.111 (3) | 0.079 (2) | 0.108 (3) | 0.029 (2) | 0.054 (2) | 0.049 (2) |
C14 | 0.073 (2) | 0.0605 (18) | 0.101 (2) | 0.0098 (15) | 0.0285 (18) | 0.0229 (17) |
C15 | 0.0555 (15) | 0.0561 (15) | 0.0644 (16) | 0.0036 (13) | 0.0068 (12) | 0.0121 (13) |
C16 | 0.0522 (14) | 0.0615 (15) | 0.0373 (11) | 0.0096 (12) | 0.0033 (10) | 0.0105 (11) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.733 (3) | C5—C6 | 1.378 (4) |
Cl2—C14 | 1.754 (4) | C5—H5 | 0.9300 |
O1—C7 | 1.240 (3) | C6—H6 | 0.9300 |
N1—C7 | 1.344 (3) | C8—C9 | 1.436 (3) |
N1—N2 | 1.393 (3) | C8—H8 | 0.9300 |
N1—H1n | 0.86 (1) | C9—C10 | 1.382 (3) |
N2—C8 | 1.275 (3) | C9—C16 | 1.437 (4) |
N3—C10 | 1.353 (4) | C10—H10 | 0.9300 |
N3—C11 | 1.364 (4) | C11—C12 | 1.390 (5) |
N3—H3n | 0.85 (1) | C11—C16 | 1.414 (3) |
C1—C6 | 1.385 (3) | C12—C13 | 1.367 (6) |
C1—C2 | 1.388 (3) | C12—H12 | 0.9300 |
C1—C7 | 1.489 (4) | C13—C14 | 1.400 (6) |
C2—C3 | 1.379 (4) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.371 (4) |
C3—C4 | 1.375 (4) | C15—C16 | 1.397 (4) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C5 | 1.378 (4) | ||
C7—N1—N2 | 120.2 (2) | N2—C8—C9 | 119.4 (2) |
C7—N1—H1n | 116.6 (19) | N2—C8—H8 | 120.3 |
N2—N1—H1n | 121.2 (19) | C9—C8—H8 | 120.3 |
C8—N2—N1 | 115.9 (2) | C10—C9—C8 | 126.0 (2) |
C10—N3—C11 | 109.4 (2) | C10—C9—C16 | 106.4 (2) |
C10—N3—H3n | 128 (3) | C8—C9—C16 | 127.6 (2) |
C11—N3—H3n | 122 (3) | N3—C10—C9 | 110.0 (3) |
C6—C1—C2 | 118.8 (2) | N3—C10—H10 | 125.0 |
C6—C1—C7 | 122.6 (2) | C9—C10—H10 | 125.0 |
C2—C1—C7 | 118.6 (2) | N3—C11—C12 | 130.8 (3) |
C3—C2—C1 | 120.5 (2) | N3—C11—C16 | 108.3 (2) |
C3—C2—H2 | 119.8 | C12—C11—C16 | 120.9 (3) |
C1—C2—H2 | 119.8 | C13—C12—C11 | 118.8 (3) |
C4—C3—C2 | 119.6 (2) | C13—C12—H12 | 120.6 |
C4—C3—H3 | 120.2 | C11—C12—H12 | 120.6 |
C2—C3—H3 | 120.2 | C12—C13—C14 | 120.2 (3) |
C3—C4—C5 | 120.9 (3) | C12—C13—H13 | 119.9 |
C3—C4—Cl1 | 119.8 (2) | C14—C13—H13 | 119.9 |
C5—C4—Cl1 | 119.3 (2) | C15—C14—C13 | 122.3 (4) |
C4—C5—C6 | 119.1 (3) | C15—C14—Cl2 | 118.7 (3) |
C4—C5—H5 | 120.4 | C13—C14—Cl2 | 119.0 (3) |
C6—C5—H5 | 120.4 | C14—C15—C16 | 118.0 (3) |
C1—C6—C5 | 121.0 (2) | C14—C15—H15 | 121.0 |
C1—C6—H6 | 119.5 | C16—C15—H15 | 121.0 |
C5—C6—H6 | 119.5 | C15—C16—C11 | 119.8 (3) |
O1—C7—N1 | 120.0 (2) | C15—C16—C9 | 134.2 (2) |
O1—C7—C1 | 121.1 (2) | C11—C16—C9 | 106.0 (2) |
N1—C7—C1 | 118.9 (2) | ||
C7—N1—N2—C8 | 175.1 (2) | C8—C9—C10—N3 | −177.9 (3) |
C6—C1—C2—C3 | −2.4 (4) | C16—C9—C10—N3 | −0.9 (3) |
C7—C1—C2—C3 | 178.4 (2) | C10—N3—C11—C12 | 180.0 (3) |
C1—C2—C3—C4 | 0.7 (4) | C10—N3—C11—C16 | −0.2 (3) |
C2—C3—C4—C5 | 1.6 (4) | N3—C11—C12—C13 | −179.0 (3) |
C2—C3—C4—Cl1 | −178.0 (2) | C16—C11—C12—C13 | 1.2 (5) |
C3—C4—C5—C6 | −2.1 (4) | C11—C12—C13—C14 | −1.7 (5) |
Cl1—C4—C5—C6 | 177.5 (2) | C12—C13—C14—C15 | 1.0 (5) |
C2—C1—C6—C5 | 1.9 (4) | C12—C13—C14—Cl2 | −178.6 (3) |
C7—C1—C6—C5 | −178.9 (2) | C13—C14—C15—C16 | 0.2 (4) |
C4—C5—C6—C1 | 0.3 (4) | Cl2—C14—C15—C16 | 179.8 (2) |
N2—N1—C7—O1 | −166.4 (2) | C14—C15—C16—C11 | −0.7 (4) |
N2—N1—C7—C1 | 13.3 (4) | C14—C15—C16—C9 | −179.9 (3) |
C6—C1—C7—O1 | −137.3 (3) | N3—C11—C16—C15 | −179.8 (2) |
C2—C1—C7—O1 | 41.9 (4) | C12—C11—C16—C15 | 0.0 (4) |
C6—C1—C7—N1 | 43.0 (4) | N3—C11—C16—C9 | −0.4 (3) |
C2—C1—C7—N1 | −137.8 (3) | C12—C11—C16—C9 | 179.5 (3) |
N1—N2—C8—C9 | −177.9 (2) | C10—C9—C16—C15 | −179.9 (3) |
N2—C8—C9—C10 | 175.8 (3) | C8—C9—C16—C15 | −3.0 (5) |
N2—C8—C9—C16 | −0.5 (4) | C10—C9—C16—C11 | 0.8 (3) |
C11—N3—C10—C9 | 0.7 (3) | C8—C9—C16—C11 | 177.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O1i | 0.86 (1) | 2.10 (1) | 2.941 (3) | 167 (3) |
N3—H3n···O1ii | 0.85 (1) | 2.13 (2) | 2.935 (3) | 157 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+1/2, z+1/2. |
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